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Quinox, a Quinoline‐Type N ‐Oxide, as Organocatalyst in the Asymmetric Allylation of Aromatic Aldehydes with Allyltrichlorosilanes: The Role of Arene–Arene Interactions
Author(s) -
Malkov Andrei V.,
Dufková Lenka,
Farrugia Louis,
Kočovský Pavel
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351737
Subject(s) - chemistry , quinoline , aldehyde , catalysis , selectivity , lewis acids and bases , combinatorial chemistry , organic chemistry
The allylation of aromatic aldehydes with allyltrichlorosilanes can be catalyzed by the new Lewis basic organocatalyst quinox with high enantioselectivity for electron‐poor aldehydes and low for their electron‐rich congeners (see scheme). This behavior suggests an arene–arene interaction of the electron‐rich catalyst with the incoming aldehyde as the main factor determining the enantiofacial selectivity.